Abstract
Conjugated dienediynes and enediynes with definite geometry have
been prepared in a one-pot manner. This protocol involves two types
of coupling reaction, a Suzuki-type coupling and either a Hay coupling
or a Cadiot-Chodkiewicz coupling. Thus, the copper-mediated
cross-coupling reaction of (E )-alk-1-enyldisiamylborane
with (trimethylsilyl)ethynyl bromide is carried out in the presence
of 1 M NaOMe to generate (E )-alk-3-en-1-yne,
which is subjected to either palladium/copper-catalyzed
homocoupling in the presence of DABCO or copper-catalyzed heterocoupling
with 1-iodoalk-1-yne in the presence of TBD or pyrrolidine in a
single reaction pot without isolating (E )-alk-3-en-1-yne.
The homocoupling has realized the stereoselective construction of
(1E ,7E )-alka-1,7-diene-3,5-diynes,
and the heterocoupling has achieved the formation of (E )-alk-1-ene-3,5-diynes. In addition,
starting from (Z )-alk-1-enyldisiamylborane
instead of the E -isomer, this series
of reactions has led to the formation of (1Z ,7Z )-alka-1,7-diene-3,5-diynes and (Z )-alk-1-ene-3,5-diynes, albeit limiting
the scope of the substrate.
Key words
alkenylborane - (trimethylsilyl)ethynyl bromide - alk-1-en-3-yne - Suzuki-type reaction - acetylenic coupling
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